Triethylamine → 4-Methyl-3-(3-(pyridin-3-yl)acrylamido)benzoic acid methyl ester

Participants

Reaction Steps

To a suspension of 3-pyridin-3-ylacryloyl chloride hydrochloride (5.1 g) in anhydrous dichloromethane (100 ml), a solution of 3-amino-4-methyl benzoic acid methyl ester (2.75 g) and triethylamine (2.3 ml) in dichloromethane (50 ml) was added dropwise slowly in an ice-bath with the temperature no more than 5° C. After addition, the reaction was carried out for 30 min in an ice-bath, and to then at room temperature for 3 h. The completion of reaction was indicated by TLC. The reaction mixture was concentrated and dissolved into 150 ml of sodium hydroxide solution (10%). The reaction mixture was extracted with EtOAc (30 ml*3). The organic layer was dried over anhydrous MgSO4, and filtered. Most EtOAc was removed by evaporation under reduced pressure. The is residue was cooled in refrigerator. Crystallization and filtration provided a light yellow crystal.

Provenance & Evidence